Trifluoroacetic acid → HCID 71267444, compound

HRID 1505797Notes

Reaction equation

HRID 1505797 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[C:10]([CH3:49])=[C:11]([NH:15][C:16]([C:18]2[C:26]3[N:25]=[C:24]([NH:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[NH:23][C:22]=3[CH:21]=[C:20]([NH:36][C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]([F:48])([F:47])[F:46])=[O:38])[CH:19]=2)=[O:17])[CH:12]=[CH:13][CH:14]=1>C(Cl)Cl>[Cl:8][C:9]1[C:10]([CH3:49])=[C:11]([NH:15][C:16]([C:18]2[C:26]3[N:25]=[C:24]([NH:27][CH2:28][C:29]([OH:31])=[O:30])[NH:23][C:22]=3[CH:21]=[C:20]([NH:36][C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]([F:46])([F:47])[F:48])=[O:38])[CH:19]=2)=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90229353HCID 90229353, compound

Product 1

HCID 71267444HCID 71267444, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl N-{4-[(3-chloro-2-methylphenyl)carbamoyl]-6-({[2-(trifluoro methyl)phenyl]carbonyl}amino)-1H-benzimidazol-2-yl}glycinate (95 mg) in methylene chloride (2 mL), and the mixture was stirred for 1 hour at room temperature, and concentrated. The residue was neutralized with 1N aqueous NaOH under ice-cooling and extracted with EtOAc. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified on column chromatography to obtain N-{4-[(3-chloro-2-methylphenyl)carbamoyl]-6-({[2-(trifluoro methyl)phenyl]carbonyl}amino)-1H-benzimidazol-2-yl}glycine (50 mg) as white powder. N-{4-[(3-chloro-2-methylphenyl)carbamoyl]-6-({[2-(trifluoro methyl)phenyl]carbonyl}amino)-1H-benzimidazol-2-yl}glycine (16 mg) was suspended in MeOH. To the suspension was added 2N hydrogen chloride/EtOH solution (1 Eq) to obtain a homogeneous solution. The solvent was removed under reduced pressure. The residue was triturated in diethyl ether, and the precipitate was collected by filtration and dried to obtain the titled compound (12 mg) as white powder.

Workup

  1. concentrationconcentrated
  2. temperaturecooling
  3. extractionextracted with EtOAc
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-cc91040a838c4edea1b2009978950ae9
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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